It’s easy to fall into the Florence trap in Tuscany. While no one is denying the appeal of that most cultured of cities, Tuscany goes way beyond the obvious appeal of Pisa’s leaning tower, Siena’s Palio and popular hill towns like San Gimignano. Read on to find out how you can sidestep the crowds and find Tuscany's off-the-radar highlights.

Getting Away in Tuscany

Go the extra mile in Tuscany and we promise you’ll find comparable treasures with only a fraction of the tourists—from tucked-away medieval towns founded by the Etruscans to pine-brushed nature reserves, little-visited beaches to beautiful valleys where olive groves and fields of poppies lift to hills stippled with cypress trees.

Once you're back in Florence, there are still ways to do it differently—see our guide for ideas. And check out our 14-day itinerary of Tuscany for more inspiration, which includes immersive activities such as truffle hunting, winery tours and pasta making classes. 

Volterra

The distinctly medieval skyline of Volterra in the glow of late afternoon 

Built high on the riches of its alabaster quarries since Etruscan times, the hill town of Volterra might just be love at first sight, with its jumble of terracotta-roofed houses, hemmed in by ramparts that peer out across the plains. In many ways this town is Tuscany in microcosm, with cobbled alleys unfurling to the Piazza dei Priori, dominated by the early 13th-century Palazzo dei Priori, with its clock tower and crenellations.

The town is a time-capsule: whether you’re pondering the ruins of its Etruscan acropolis, its Roman amphitheater (one of Italy's best preserved), or its rich stash of Etruscan funerary urns at the Museo Etrusco Guarnacci. The town’s medieval cathedral appears unassuming on the face of things, but step inside and you’ll be blown away by the lavishness of its gilded coffered ceiling.

Should you choose to stay the night, a great pick is family-run organic farm Diacceroni.

Parco Regionale della Maremma

The wild, empty sands of Marina di Alberese

For solitude and breezy sea views, this regional nature park in the Maremma region of southern Tuscany can't be beat. You can hike undisturbed here through pine and silver-green olive groves, and along coastlines fringed with sweet-scented macchia (Mediterranean scrub comprising of juniper, strawberry, heather, myrtle, and broom).

Stop by the visitor center in Alberese for the inside scoop on guided walks in the park, which include a memorable one to the compelling ruins of San Rabano, a 10th-century Benedictine monastery. Bicycle and canoe tours are other options for exploring. And the beaches here are some of the wildest and quietest in Italy—take the four-mile Marina di Alberese, awash with driftwood, or the next cove along, Cala di Forno.

Alberese is a good base for exploring: try a simple-but-charming farm stay at Le Frasche.

Lucca

The gateway to Piazza Anfiteatro, Lucca

Ah, Lucca! Every bit as lovely as Siena or Florence (perhaps more so, but whisper it quietly) this ravishing medieval town has a history that runs deep. The historic center is filled with churches, galleries, and Roman ruins, yet it receives just a trickle of tourists by comparison. It's easy to reach, too: just a half-hour’s drive or train ride north of Pisa.

Right at its heart, Lucca has one of the most impressive piazzas in whole Italy: the circular Piazza Anfiteatro, built above the former Roman amphitheater and rimmed with tall lemon-colored houses and pavement cafes. The center is encircled by mighty Renaissance city walls, designed by none other than Leonardo Da Vinci himself, which are great for a panoramic walk.

Climb to the top of the redbrick, oak-tree topped Torre Guinigi for views out over Lucca to the hills beyond. Another must-see is the Romanesque cathedral, whose ornate façade conceals masterpieces such as Tintoretto’s Last Supper.

You can easily spend a couple of days just exploring Lucca—perhaps staying overnight, say, at Palazzo di Pinto, a medieval palace turned boutique hotel.

Monte Argentario 

View of Porto Ercole and its harbor in Monte Argentario 

Some might swoon over the coastlines of Capri and Amalfi, but they don’t know what they're missing in Tuscany. Midway between Rome and Pisa, Monte Argentario is the region at its rugged, rocky best. Cliffs draped in fragrant Mediterranean scrub, pine, and olive trees drop to the sea.

Linked to the mainland by three sandbars, the peninsula (almost an island, in fact) has some terrific beaches and coves to seek out, such as white-pebble Cala del Gesso on the west coast, reached by a flight of steps, and family friendly Cala Piccola. Others can only be approached by boat or a long, sweaty hike. Snorkeling and scuba diving are also big here.

A snaking coastal road rims the peninsula, forcing you to screech to a halt frequently because of the spectacular views. The main bases are the rather ritzy harbor towns of Porto Ercole, in the south, and Porto San Stefano in the north, both topped by 16th-century Spanish fortresses. These are prime spots to kick back with cocktails, try local seafood and people watch.

The swankiest address? Il Pellicano, without a doubt.

Città del Tufo

Pitigliano, a town built on tufa rock

One of the most extraordinary archaeological oddities in Tuscany is the Città del Tufo, a trio of villages (Pitigliano, Sovana, and Sorano) rising abruptly from the volcanic tufa rock. These dramatic hilltop villages have medieval centers that have been beautifully preserved, with cobbled alleys, arched lanes, staircases and lookouts to explore.

For the best views and photo ops of Pitigliano, head to the synagogue-topped Jewish quarter. From Pitigliano, a seven-mile walk threads through Etruscan-era sunken roads called Via Cave, some of which are as deep as 65 feet, to the equally pretty tufa-stone village of Sovana. This once-sacred route hides a number of Etruscan necropolises. To see cave dwellings that have been hewn directly from the rock, visit San Rocco in Sorano

Big on historic charm, La Casa degli Archi is an atmospheric place to stay, as is Hotel della Fortezza, nestled in the walls of a 12th-century castle.

Strada del Vino e dell’Olio 

The vineyards of Bolgheri 

Chianti is not the only region in Tuscany to produce excellent wines. The Wine and Olive Oil Route is a 93-mile ramble along the Etruscan coast, from Livorno to Piombino, taking in the full spectrum of Tuscany's landscapes—from vineyards to pine-backed beaches, olive groves to sunflower fields. Here you'll stumble across plenty of family-run cantine (wine cellars), many open to the public for tastings of full-bodied red and zesty white wines. 

Bolgheri is a major stop on the route for indulging in all things wine related. Drive along the Viale dei Cipressi, a sweeping avenue lined with cypress trees, to reach this medieval village entered via a castle gate. Edging south, the hilltop hamlet of Castagneto Carducci produces excellent wines and extra-virgin olive oils. 

Further south is Suvreto, another ludicrously pretty village, home to the eye-catching Mario Botta-designed winery, Petra.

Val di Chiana Aretina

Flowers bring color and scent to the backstreets of Cortona in summer

Far less visited than its Sienese counterpart, the stretch of the Val di Chiana that runs south of Arezzo is delightful, giving you a classic taste of Tuscany in gently undulating hills, olive groves, and fields where Italy’s prized Chianina cattle graze—yes, the famous Florentine T-bone hails from here.

Begin a road trip here in Arezzo, whose sloping Piazza Grande, overlooked by the Renaissance Palazzo delle Logge, provided a cinematic backdrop in Roberto Benigni’s 1997 movie Life is Beautiful. The Basilica di San Francesco harbors a true art treasure: Piero della Francesca’s fresco cycle of the Legend of the True Cross.

Make a stop, then, in the walled town of Castiglion Fiorentino, crowned by the hefty Cassero fortress. The town stages its own (smaller) version of Siena’s medieval Palio horse race on the third Sunday in June.

Fairest of all, however, is Cortona, a warren of narrow alleys, cobbles and honey-colored stone houses, which played a starring role in the 2003 movie Under the Tuscan Sun. For soul-stirring views, clamber up to the remains of the Medici fortress, and get a history fix at the Etruscan Academy Museum of Cortona.

Should you wish to spend the night here—in a Renaissance palace, no less—Hotel San Michele fits the bill nicely.

Map

Map of Tuscany Off the Beaten Path: 7 Ways to Go Beyond Florence
Map of Tuscany Off the Beaten Path: 7 Ways to Go Beyond Florence